Perylene Bisimide Cyclophane

  • Author: Jonathan Faiz
  • Published Date: 23 June 2015
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Perylene Bisimide Cyclophane

Macrocylic molecules comprising large functional π systems are of particular interest as they can accommodate large organic guest molecules such as dyes or organic semiconductors. Frank Würthner and Peter Spenst, University of Würzburg, Germany, have synthesized cyclophanes comprising two perylene bisimide (PBI) units with para-xylene bridges. This molecular design overcomes the problem that short spacers do not provide sufficient space for guest molecules and that long flexible spacers result in aggregation of the PBI units.

The PBI cyclophane was tested as a host for both electron-rich and electron-poor organic molecules. The researchers found that complexation of electron-rich guests (such as carbazole) resulted in fluorescence quenching of the host, whereas complexation of electron-poor guests (such as phenylnaphthalene) resulted in a complex with a higher quantum yield than the host.

Binding studies showed that guests with more carbon–carbon double bonds bound more strongly to the host. This system has an ideal interchromophoric distance for the effective binding of a range of hydrocarbons, and thus can be used as a "turn-off" and "turn-on" sensor for electron-rich and electron-poor hydrocarbons.


Article Views: 3956

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH